IP Library › Granted Patent US 12,733,333

Granted Patent B2

US 12,733,333 · App. 17/957,282 · Granted Sep 8, 2026

Organic light emitting diode and organic light emitting device having thereof

Inventors: Ku-Sun Choung (Paju-si, KR); Han-Sol Park (Paju-si, KR); Yoo-Jeong Jeong (Paju-si, KR)

Assignee: LG Display Co., Ltd.

H10K50/12 H10K50/15 H10K50/16 H10K85/342 H10K85/615 H10K85/622 H10K85/633 H10K85/636 H10K85/6572 H10K85/6574

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Quick Facts

Patent No.: US 12,733,333
App. No.: 17/957,282
Granted: Sep 8, 2026
Kind: B2

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Abstract

The present disclosure relates to an organic light emitting diode (OLED) in which at least one emitting material layer includes a dopant having the following structure of Formula 1 and a biscarbazole-based material and/or an azine-based material, at least one hole transport layer includes a spiro-bifluorene-based material and at least one electron transport layer includes a benzimidazole-based material, and an organic light emitting device including the OLED. The OLED and the organic light emitting device including the host and the dopant can improve their luminous efficiency and luminous lifespan.

Claims (234)

1 . An organic light emitting diode including:

a first electrode;

a second electrode facing the first electrode; and

an emissive layer disposed between the first and second electrodes, and including at least one emitting material layer, at least one hole transport layer disposed between the first electrode and the at least one emitting material layer, and at least one electron transport layer disposed between the at least one emitting material layer and the second electrode,

wherein the at least one emitting material layer includes:

a host including:

a first host represented by a structure of Formula 7, and

a second host represented by a structure of Formula 9, and

a dopant including an organometallic compound represented by a structure of Formula 1,

wherein the at least one hole transport layer includes an organic compound represented by a structure of Formula 11, and

wherein the at least one electron transport layer includes an organic compound represented by structure of Formula 15,

wherein:

Formula 1 is:

wherein, in Formula 1,

L A has a structure represented by a structure of Formula 2;

L B is an auxiliary ligand represented by a structure of Formula 5A or Formula 5B;

m is 1, 2 or 3;

n is 0, 1 or 2; and

m+n is 3;

Formula 2 is:

where in Formula 2,

each of X 1 and X 2 is independently CR 7 or N;

each of X 3 to X 5 is independently CR 8 or N and at least one of X 3 to X 5 is CR 8 ;

each of X 6 to X 9 is independently CR 9 or N and at least one of X 6 to X 9 is CR 9 ;

each of R 1 to R 9 is independently protium, deuterium, an unsubstituted or substituted C 1 -C 20 alkyl, an unsubstituted or substituted C 1 -C 20 hetero alkyl, an unsubstituted or substituted C 2 -C 20 alkenyl, an unsubstituted or substituted C 2 -C 20 hetero alkenyl, an unsubstituted or substituted C 1 -C 20 alkoxy, a carboxylic group, a nitrile, an isonitrile, a sulfanyl, a phosphine, an unsubstituted or substituted C 1 -C 20 alkyl amino, an unsubstituted or substituted C 1 -C 20 alkyl silyl, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 hetero alicyclic group, an unsubstituted or substituted C 6 -C 30 aromatic group or an unsubstituted or substituted C 3 -C 30 hetero aromatic group, and where each R 6 is identical to or different from each other when b is 2, 3 or 4;

optionally,

two adjacent R moieties among R 1 to R 5 , and/or

two adjacent R 6 when b is 2, 3 or 4, and/or

X 3 and X 4 or X 4 and X 5 , and/or

X 6 and X 7 , X 7 and X 8 , or X 8 and X 9

are further linked together to form an unsubstituted or substituted C 4 -C 20 alicyclic ring, an unsubstituted or substituted C 3 -C 20 hetero alicyclic ring, an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring;

a is 0, 1 or 2; and

b is 0, 1, 2, 3 or 4,

Formula 5A or Formula 5B is:

where in Formulae 5A and 5B,

each of R 21 , R 22 and R 31 to R 33 is independently protium, deuterium, unsubstituted or substituted C 1 -C 20 alkyl, unsubstituted or substituted C 1 -C 20 hetero alkyl, unsubstituted or substituted C 2 -C 20 alkenyl, unsubstituted or substituted C 2 -C 20 hetero alkenyl, unsubstituted or substituted C 1 -C 20 alkoxy, a carboxylic group, nitrile, isonitrile, sulfanyl, phosphine, unsubstituted or substituted C 1 -C 20 alkyl amino, unsubstituted or substituted C 1 -C 20 alkyl silyl, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 hetero alicyclic group, an unsubstituted or substituted C 6 -C 30 aromatic group or an unsubstituted or substituted C 3 -C 30 hetero aromatic group;

optionally,

two adjacent R 21 when f is 2, 3 or 4, and/or

two adjacent R 22 when g is 2, 3 or 4, and/or

R 31 and R 32 or R 32 and R 33

each of f and g is 0, 1, 2, 3 or 4,

Formula 7 is:

wherein, in Formula 7,

each of R 41 to R 44 is independently an unsubstituted or substituted C 6 -C 30 aryl or an unsubstituted or substituted C 3 -C 30 hetero aryl, where each R 43 is identical to or different from each other when p is 2, 3, 4, 5, 6 or 7 and each R 44 is identical to or different from each other when q is 2, 3, 4, 5, 6 or 7, optionally, each of the unsubstituted or substituted C 6 -C 30 aryl and the unsubstituted or substituted C 3 -C 30 hetero aryl independently forms a spiro structure with an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring; and

each of p and q is independently 0, 1, 2, 3, 4, 5, 6 or 7,

Formula 9 is:

where in Formula 9,

each of R 51 and R 52 is independently unsubstituted or substituted C 6 -C 30 aryl or unsubstituted or substituted C 3 -C 30 hetero aryl;

R 53 is hydrogen or unsubstituted or substituted C 6 -C 30 aryl, optionally, the unsubstituted or substituted C 6 -C 30 aryl forms a spiro structure with an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring;

L is a single bond, unsubstituted or substituted C 6 -C 30 arylene or unsubstituted or substituted C 3 -C 30 hetero arylene, optionally, each of the unsubstituted or substituted C 6 -C 30 arylene and the unsubstituted or substituted C 3 -C 30 hetero arylene independently forms a spiro structure with an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring;

each of Y 1 , Y 2 and Y 3 is independently CR 54 or N, wherein at least one of Y 1 , Y 2 and Y 3 is N;

R 54 is independently hydrogen, unsubstituted or substituted C 6 -C 30 aryl or unsubstituted or substituted C 3 -C 30 hetero aryl, optionally, each of the unsubstituted or substituted C 6 -C 30 aryl and the unsubstituted or substituted C 3 -C 30 hetero aryl independently forms a spiro structure with an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring; and

Z is O or S,

Formula 11 is:

where in Formula 11,

each of R 61 and R 62 is independently an unsubstituted or substituted C 6 -C 30 aryl or an unsubstituted or substituted C 3 -C 30 hetero aryl, wherein at least one of R 61 and R 62 is polycyclic aryl or polycyclic hetero aryl, optionally, each of the unsubstituted or substituted C 6 -C 30 aryl and the unsubstituted or substituted C 3 -C 30 hetero aryl independently forms a spiro structure with an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring;

each of R 63 to R 66 is independently an unsubstituted or substituted C 1 -C 20 alkyl or an unsubstituted or substituted C 6 -C 30 aryl, wherein each R 63 is identical to or different from each other when r is 2, 3 or 4, each R 64 is identical to or different from each other when s is 2, 3 or 4, each R 65 is identical to or different from each other when t is 2, 3 or 4, and each R 66 is identical to or different from each other when u is 2, 3 or 4;

each of L 1 to L 3 is independently a single bond, an unsubstituted or substituted C 6 -C 30 arylene or an unsubstituted or substituted C 3 -C 30 hetero arylene, optionally, each of the unsubstituted or substituted C 6 -C 30 arylene and the unsubstituted or substituted C 3 -C 30 hetero arylene independently forms a spiro structure with an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring; and

each of r, s, t and u is independently 0, 1, 2, 3 or 4,

Formula 15 is:

where in Formula 15,

R 72 is ethyl;

R 73 is hydrogen;

R 74 is phenyl; and

Ar 1 is anthracenylene.

2 . The organic light emitting diode of claim 1 , wherein L A has the following structure of Formula 4A or Formula 4B:

wherein, in Formulae 4A and 4B,

each of R 1 to R 6 and b is a same as defined in Formula 2;

each of R 11 to R 14 is independently protium, deuterium, an unsubstituted or substituted C 1 -C 20 alkyl, an unsubstituted or substituted C 1 -C 20 hetero alkyl, an unsubstituted or substituted C 2 -C 20 alkenyl, an unsubstituted or substituted C 2 -C 20 hetero alkenyl, an unsubstituted or substituted C 1 -C 20 alkoxy, a carboxylic group, a nitrile, an isonitrile, a sulfanyl, a phosphine, an unsubstituted or substituted C 1 -C 20 alkyl amino, an unsubstituted or substituted C 1 -C 20 alkyl silyl, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 hetero alicyclic group, an unsubstituted or substituted C 6 -C 30 aromatic group or an unsubstituted or substituted C 3 -C 30 hetero aromatic group;

optionally,

two adjacent R 13 when d is 2 or 3, and/or

two adjacent R 14 when e is 2, 3 or 4

c is 0 or 1;

d is 0, 1, 2 or 3; and

e is 0, 1, 2, 3 or 4.

3 . The organic light emitting diode of claim 1 , wherein L A has the following structure of Formula 4C or Formula 4D:

where in Formulae 4C and 4D,

each of R 1 to R 6 and b is as defined in Formula 2;

optionally,

two adjacent R 13 when d is 2 or 3, and/or

two adjacent R 14 when e is 2, 3 or 4

c is 0 or 1;

d is 0, 1, 2 or 3; and

e is 0, 1, 2, 3 or 4.

4 . The organic light emitting diode of claim 1 , wherein X 1 is CR 7 , X 2 is CR 7 or N, each of X 3 to X 5 is independently CR 8 and each of X 6 to X 9 is independently CR 9 .

5 . The organic light emitting diode of claim 1 , wherein the emissive layer includes:

a first emitting part disposed between the first and second electrodes and including a first emitting material layer;

a second emitting part disposed between the first emitting part and the second electrode and including a second emitting material layer; and

a first charge generation layer disposed between the first and second emitting parts,

wherein the first emitting part includes a first emitting material layer, a first hole transport layer disposed between the first electrode and the first emitting material layer, and a first electron transport layer disposed between the first emitting material layer and the first charge transport layer,

wherein the second emitting part includes a second emitting material layer, a second hole transport layer disposed between the first charge generation layer and the second emitting material layer, and a second electron transport layer disposed between the second emitting material layer and the second electrode,

wherein at least one of the first emitting material layer and the second emitting material layer includes the host and the dopant,

wherein at least one of the first hole transport layer and the second hole transport layer includes the organic compound represented by the structure of Formula 11, and

wherein at least one of the first electron transport layer and the second electron transport layer includes the organic compound represented by the structure of Formula 15.

6 . The organic light emitting diode of claim 5 , wherein the second emitting material layer includes:

a first layer disposed between the second hole transport layer and the second electron transport layer; and

a second layer disposed between the first layer and the second electron transport layer,

wherein one of the first layer and the second layer includes the host and the dopant,

wherein the second hole transport layer includes the organic compound represented by the structure of Formula 11, and

wherein the second electron transport layer includes the organic compound represented by the structure of Formula 15.

7 . The organic light emitting diode of claim 6 , wherein the second emitting material layer further includes a third layer disposed between the first layer and the second layer.

8 . The organic light emitting diode of claim 5 , wherein the emissive layer further includes:

a third emitting part disposed between the second emitting part and the second electrode and including a third emitting material layer, and

a second charge generation layer disposed between the second and third emitting parts, and

wherein the third emitting part includes a third emitting material layer, a third hole transport layer disposed between the second charge generation layer and the second emitting material layer, and a third electron transport layer disposed between the third emitting material layer and the second electrode.

9 . The organic light emitting diode of claim 8 , wherein the second emitting material layer includes:

a first layer disposed between the second hole transport layer and the second electron transport layer; and

a second layer disposed between the first layer and the second electron transport layer,

wherein one of the first layer and the second layer includes the host and the dopant,

wherein the second hole transport layer includes the organic compound represented by the structure of Formula 11, and

wherein the second electron transport layer includes the organic compound represented by the structure of Formula 15.

10 . An organic light emitting device, including:

a substrate; and

the organic light emitting diode of claim 1 disposed over the substrate.

11 . The organic light emitting diode of claim 1 , wherein the organometallic compound is selected from:

12 . The organic light emitting diode of claim 1 , wherein the organic compound having the structure represented by Formula 11 includes:

13 . The organic light emitting diode of claim 1 , wherein the organic compound having the structure represented by Formula 15 includes:

14 . The organic light emitting diode of claim 1 , wherein the first host having the structure represented by Formula 7 includes:

15 . The organic light emitting diode of claim 1 , wherein the second host having the structure represented by Formula 9 includes:

16 . An organic light emitting diode including:

a first electrode;

a second electrode facing the first electrode; and

an emissive layer disposed between the first and second electrodes,

wherein the emissive layer includes:

a first emitting part disposed between the first and second electrodes and including a blue emitting material layer;

a second emitting part disposed between the first emitting part and the second electrode; and

a first charge generation layer disposed between the first and second emitting parts,

wherein the second emitting part includes:

at least one emitting material layer;

a hole transport layer disposed between the first charge generation layer and the at least one emitting material layer;

and an electron transport layer disposed between the at least one emitting material layer and the second electrode,

wherein the at least one emitting material layer includes:

a host including:

a first host represented by a structure of Formula 7, and

a second host represented by a structure of Formula 9, and

a dopant including an organometallic compound represented by a structure of Formula 1,

wherein the hole transport layer includes an organic compound represented by a structure of Formula 11, and

wherein the electron transport layer includes an organic compound represented by a structure of Formula 15:

wherein:

Formula 1 is:

wherein, in Formula 1,

L A has a structure represented by a structure of Formula 2;

L B is an auxiliary ligand represented by a structure of Formula 5A or Formula 5B;

m is 1, 2 or 3;

n is 0, 1 or 2; and

m+n is 3;

Formula 2 is:

where in Formula 2,

each of X 1 and X 2 is independently CR 7 or N;

each of X 3 to X 5 is independently CR 8 or N and at least one of X 3 to X 5 is CR 8 ;

each of X 6 to X 9 is independently CR 9 or N and at least one of X 6 to X 9 is CR 9 ;

optionally,

two adjacent R moieties among R 1 to R 5 , and/or

two adjacent R 6 when b is 2, 3 or 4, and/or

X 3 and X 4 or X 4 and X 5 , and/or

X 6 and X 7 , X 7 and X 8 , or X 8 and X 9

a is 0, 1 or 2; and

b is 0, 1, 2, 3 or 4,

Formula 5A or Formula 5B is:

where in Formulae 5A and 5B,

optionally,

two adjacent R 21 when f is 2, 3 or 4, and/or

two adjacent R 22 when g is 2, 3 or 4, and/or

R 31 and R 32 or R 32 and R 33

each of f and g is 0, 1, 2, 3 or 4,

Formula 7 is:

wherein, in Formula 7,

each of p and q is independently 0, 1, 2, 3, 4, 5, 6 or 7,

Formula 9 is:

where in Formula 9,

each of R 51 and R 52 is independently unsubstituted or substituted C 6 -C 30 aryl or unsubstituted or substituted C 3 -C 30 hetero aryl;

each of Y 1 , Y 2 and Y 3 is independently CR 54 or N, wherein at least one of Y 1 , Y 2 and Y 3 is N;

Z is O or S,

Formula 11 is:

where in Formula 11,

each of R 63 to R 66 is independently an unsubstituted or substituted C 1 -C 20 alkyl or an unsubstituted or substituted C 6 -C 30 aryl, wherein each R 63 is identical to or different from each other when r is 2, 3 or 4, each R 64 is identical to or different from each other when s is 2, 3 or 4, each R 65 is identical to or different from each other when tis 2, 3 or 4, and each R 66 is identical to or different from each other when u is 2, 3 or 4;

each of r, s, t and u is independently 0, 1, 2, 3 or 4,

Formula 15 is:

where in Formula 15,

R 72 is ethyl;

R 73 is hydrogen;

R 74 is phenyl; and

Ar 1 is anthracenylene.

17 . The organic light emitting diode of claim 16 , wherein L A has the following structure of Formula 4A or Formula 4B:

wherein, in Formulae 4A and 4B,

each of R 1 to R 6 and b is a same as defined in Formula 2;

optionally,

two adjacent R 13 when d is 2 or 3, and/or

two adjacent R 14 when e is 2, 3 or 4

c is 0 or 1;

d is 0, 1, 2 or 3; and

e is 0, 1, 2, 3 or 4.

18 . The organic light emitting diode of claim 16 , wherein L A has the following structure of Formula 4C or Formula 4D:

where in Formulae 4C and 4D,

each of R 1 to R 6 and b is as defined in Formula 2;

optionally,

two adjacent R 13 when d is 2 or 3, and/or

two adjacent R 14 when e is 2, 3 or 4

c is 0 or 1;

d is 0, 1, 2 or 3; and

e is 0, 1, 2, 3 or 4.

19 . The organic light emitting diode of claim 16 , wherein X 1 is CR 7 , X 2 is CR 7 or N, each of X 3 to X 5 is independently CR 8 and each of X 6 to X 9 is independently CR 9 .

20 . The organic light emitting diode of claim 16 , wherein the at least one emitting material layer includes:

a first layer disposed between the hole transport layer and the electron transport layer, and including a red emitting material layer; and

a second layer disposed between the first layer and the electron transport layer, and including the host and the dopant.

21 . The organic light emitting diode of claim 20 , wherein the at least one emitting material layer further includes a third layer disposed between the first layer and the second layer, and wherein the third layer includes a yellow green emitting material layer.

22 . The organic light emitting diode of claim 16 , wherein the emissive layer further includes:

a third emitting part disposed between the second emitting part and the second electrode and including a blue emitting material layer; and

a second charge generation layer disposed between the second and third emitting parts.

23 . The organic light emitting diode of claim 22 , wherein the at least one emitting material layer includes:

a first layer disposed between the hole transport layer and the electron transport layer, and including a red emitting material layer; and

a second layer disposed between the first layer and the electron transport layer, and including the host and the dopant.

24 . The organic light emitting diode of claim 23 , wherein the at least one emitting material layer further includes a third layer disposed between the first layer and the second layer, and wherein the third layer includes a yellow green emitting material layer.

25 . An organic light emitting device, including:

a substrate; and

the organic light emitting diode of claim 16 disposed over the substrate.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 30, 2022

From: CHOUNG, KU-SUN; PARK, HAN-SOL; JEONG, YOO-JEONG

To: LG DISPLAY CO., LTD.

Reel/Frame 061277/0768 →

Priority Claims (1)

KR 10-2021-0165809 · Nov 26, 2021 · national

Continuity (1)

Related Publication 20230171978A1 · Jun 1, 2023

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